When actress Diane Keaton stepped onto the set of the 1977 film Annie Hall, she did so in her own clothes—a collection of oversized, thrifted menswear that would go on to define an era. The now-iconic look—featuring slouchy tweed jackets, wide-leg trousers, vests, and neckties—was born from a surprising personal anxiety, a choice that the film’s director, Woody Allen, and costume designer initially opposed, only to watch it become one of cinema’s most enduring fashion revolutions.
The Personal Anxiety Behind the Pants
Keaton’s decision to forgo the typical feminine dresses and skirts of the time was not initially a grand fashion statement, but a protective measure rooted in self-consciousness. The Problem: Diane Keaton has publicly stated that she was insecure about her legs and felt uncomfortable exposing them. She found refuge in loose-fitting, covering garments—the antithesis of typical Hollywood feminine attire. The Wardrobe: Her style, which she insisted on wearing for the role of Annie Hall, was a reflection of her personal, real-life wardrobe. It was an androgynous mix inspired by the great screen stars of the 1930s and ’40s.
Directorial Pushback and Costume Clash
The bold, masculine aesthetic immediately caused friction with the creative team, who envisioned a more conventional look for the romantic lead. Fact: Both Woody Allen, the film’s writer and director, and costume designer Ruth Morley initially tried to persuade Keaton to change her mind. They reportedly suggested she wear more form-fitting jeans or skirts, believing the baggy menswear was too distracting or simply not flattering for a leading lady. The Resolve: Keaton was famously resolute, arguing that the clothes were essential to her authentic portrayal of the quirky, independent Annie Hall. She prevailed, and her personal style became a foundational element of the character.
The Enduring Fashion Revolution
The success of Annie Hall, which won the Academy Award for Best Picture, cemented the character’s look in the cultural lexicon. What started as a coping mechanism for personal insecurity became a profound style movement. The Impact: The “Annie Hall Look” immediately crossed over into mainstream fashion. It popularized the concept of androgynous dressing for women, empowering them to embrace traditionally male garments—blazers, vests, and especially wide-leg trousers—as symbols of confidence and unconventional femininity. Diane Keaton herself won the Academy Award for Best Actress for the role of Annie Hall, an achievement inextricably linked to the distinct personality and style she brought to the screen. The legacy of the Annie Hall wardrobe demonstrates how personal conviction, even if driven by insecurity, can override conventional wisdom and ultimately lead to monumental cultural change, influencing fashion trends for generations to follow.